Stiles has been excited for today ever since Derek and the rest of the frat guys told him about it. They've got a nice money making system in place, helps curb the costs of school not covered for their scholarship brothers, helps fund the parties and upkeep on the house. There was only the barest bit of hesitancy about his face being on camera, but he got over it pretty quick when the brothers showed him the extensive collection from past years and he saw some pretty recognizable (and successful) men among the performers. And now it's time, his debut in amateur porn.
Stiles heads down to the basement, a little shocked at the state of it - the nicer furniture has been moved out and ratty pieces brought in instead. There are solo cups and beer cans and bottles scattered around, little piles of laundry here and there. He's pretty sure his face conveys his confusion because Derek laughs a little when he catches sight of him and heads over.
“It’s amateur frat porn, people expect it to look like a typical frat house.” It's said with a smirk and a gesture at the pseudo-mess, and Stiles gets it, because it does look like every cliched frat house he's seen in movies, and he says so out loud. “Yeah, well, it's not the only cliche that's coming today.” Derek's laughter and eyebrow waggle has Stiles joining him, darting in for a quick kiss before allowing Derek to lead him over to the other guys and their makeshift “wardrobe”. He strips down quickly, taking the offered jock, gym shorts, and ratty tank from Mark, one of the senior brothers. He's bent over, pulling on the shorts, when there's the thud of more feet on the stairs. Stiles is a little puzzled by it, because he knows it was supposed to be him and four of the older brothers - Derek, Mark, Brian, and Cam. They're all here, so he twists his head as he straightens and is shocked to find Jackson standing at the bottom of the steps.
“What?” Jackson's bitchface is nothing new, and neither is the attitude. Stiles is about to snap back when there's a hand on his shoulder, and then Derek is moving past him.
“Changed your mind?” Jackson flushes and his head drops a bit, tilts until he's looking up at them from under his lashes. Derek's in front of him now, and whatever Jackson says in reply has him smiling. The change in demeanor is surprising. It's even more surprising when Jackson leans forward and drags Derek into a kiss. Of all the newer brothers who could join them, Jackson wasn't even on Stiles’ radar. He hadn't seen much of him since the welcome party a month ago,was pretty sure he'd left the frat in fact. But apparently Stiles had been wrong.
Really wrong. Stiles can see the eager way Jackson is sucking at Derek's mouth, the tiny tremors wracking him as Derek's hands pull at Jackson's hips, dragging him in, the way he ruts against Derek's meaty thigh. He can hear the faint whimpers Jackson is making too. Stiles doesn't realize he's palming his own cock until Brian calls over for everyone to save it for the cameras. Stiles can't believe he'd ever have found anything Jackson did as hot (and that's a dirty lie - he always found him hot, it's just that his personality was enough to nip any interest in the ass). Stiles’ hand is still holding onto his cock when Jackson and Derek separate, Derek looking smug and Jackson looking less bitchy. He can see a faint sheen of sweat on Jackson's face, the rapid rise and fall of his chest. Derek heads back towards the makeshift wardrobe and Jackson starts that way before changing direction and stepping over to Stiles.
“Sorry,” it's not quite a mumble, and Jackson doesn't look at him when he says it, but Stiles didn't expect even that much so he just nods and pats him awkwardly on the back before steering him over to be given something to wear. Stiles leans against the arm of one of the sofas while everyone else gets ready. Jackson is dressed like the rest of the guys, the kind of preppy douchebags that you'd expect in a frat filled with rich kids and jocks. Stiles knew the plan when it was just him - wannabe pledge doing what it took to get in with the rich kids. He was ready to deal with four cocks in his face and ass, he supposes one more won't really make a difference. He can see Cam setting up the rest of the room, leaving lube, unopened beers, and a few other props everywhere. Brian is checking the cameras - they've got some anchored in the walls, a few freestanding, and a couple of handhelds. They have a friend who does all the editing, so all they need is plenty of angles.
It doesn't take long to finish the set-up and get started. They didn't script any dialogue, had only the vaguest outline of what was going to happen. Derek gave them all the safeword in case they weren't on board with what was happening, and that was pretty much it. Stiles kinda wishes he'd asked what Jackson's role would be, but as soon as they were ready, Jackson had jogged back up the stairs to wait for some cue. Stiles took a deep breath and smiled over at Derek, he got a wink in return and then the red recording lights popped on around them.
The seniors were spread out across two sofas set to face each other, enough space for someone to get down on their hands and knees. The guys were kicked back and joking while Stiles went to town. He was alternating between Mark and Cam, sucking down first one then the other, damn near gagging himself on their cocks. Behind him, his gym shorts had been yanked below his ass cheeks so Derek and Mark could take turns playing with his hole. Stiles has been at it awhile, switching between all four guys whenever someone taps his hips. He's mostly tuned out on the filth they've been aiming at him, worried that if he hears them talk about how hot it is that he's so easy for them then he'll blow his load. He's trying to hold out as long as he can, even though he knows he can go at least twice.
He's been on his hands and knees for at least a half hour when he feels a new sensation probing against his hole. He pulls off of Cam's cock long enough to look over his shoulder. He can see Mark sitting at an angle to spread his cheeks wide, but it's Derek, leaned back and smirking that draws his attention. He's got one leg pulled up and hovering, and Stiles can identify the new sensation as soon as he sees it. Can feel himself being shallowly penetrated by something thick and wide and short.
“Like that? Like me fucking your greedy little hole with my dirty toes? I thought so.” Stiles has to reach down and clamp a hand around himself when he feels his cock pulse in time with the toe sliding in and out of him. He turns back to the guys in front of him, switches over to Brian's cock and tries to focus. He can see Cam lift his cell phone and text someone before dropping it back onto the cushions. It's out of Stiles’ mind when he drops his head all the way down, nose buried in Brian's pubes. He's rocking back and forth between Derek's toes in his ass and Brian's cock down his throat when he hears the door at the top of the stairs open, hears Jackson's voice over the slick noises coming from all of them.
“Hey, I got the text about initiation,” Jackson is already bouncing down the stairs, his voice trailing off for a second before returning with mock incredulity, “what the fuck is going on? Is that - what?” Stiles is surprised at the hunger he can hear in Jackson's tone.
“Initiation.” Derek's face probably looks as smug as he sounds, punctuating his answer with another thrust of his toe inside of Stiles, the other ones flexing against his rim. He pulls off of Brian with a lewd pop and drags his tingling mouth into a smirk as he twists again to look over his shoulder.
“Jealous?” And god, his voice is wrecked. Hoarse from too much battering. He loves it. Jackson's brows go up at the question, mouth hanging open slightly before he makes a noise somewhere between a growl and a moan and the next thing Stiles knows, Jackson is tearing off the polo he'd been wearing and dropping to the floor by Stiles’ ass. He knocks Mark's hands out of the way and drapes what feels like half his body over Stiles lower back, yanking his cheeks farther apart than they had been and bending down. Stiles jolts at the glob of spit that hits his pucker, then faceplants in Brian's crotch when Jackson follows it with his own tongue. There's a hungry sound and then Jackson is sloppily licking and sucking at Stiles’ hole around Derek's foot, trying to fuck his tongue in alongside Derek's toe. Stiles feels it when Derek draws all the way back out, can hear Jackson turn his attention briefly on Derek's foot before he buries his tongue back inside of Stiles.
It's quite possibly the filthiest thing Stiles has experienced yet, and he loves it. He allows himself another minute of enjoying the way Jackson is devouring his ass before he gets back to sucking Brian's cock. Stiles let's the drool run out of his mouth, coating Brian's cock, is more than happy to let Brian hold his head in place and start fucking up, his eyes streaming every time the cockhead hits the back of his throat. He can hear a bit of laughter and joking coming from behind him, Derek and Mark commenting on how hungry Jackson is for Stiles’ tight ass, how eager to suck on their feet whenever they prod at Stiles’ hole with their toes. He hears them start talking about just how thirsty Jackson must be after all that work and he gets curious, drags his head back until Brian gets the message and lets go, drifts his face down to mouth at Brian's hairy sac instead so he can focus better on what's going on behind him.
“How's that sound Jacks? You getting thirsty? Wanna wet your throat with one of these nice cold beers?” Stiles looks over his shoulder again, watches Mark pop the cap on one of the beer bottles they'd set up around the room. Watching helps him not startle too much when the bottle gets tipped over the top of his ass, cold beer running down the cleft between his cheeks. Jackson moans when the cool liquid hits Stiles’ hole where his tongue is buried, and Stiles can't stop himself from joining the sound with one of his own as Jackson laps at his twitching rim. He feels another cold burst and doesn't stop his body from arching his ass up higher, slowing the path of the liquid, shivering a little at the cold sensation against his overheated pucker. He watches as Derek stops Mark's arm when he reaches forward to drop a third splash over Stiles.
“I have a better idea.” There's a mischievous glint to Derek's eye, and Stiles wants to ask what's got him suddenly so much more interested, but he doesn't get a chance before Derek is leaning forward to scoop him up. He may or may not make a squeak as he's yanked into Derek's lap, but it doesn't last long, Derek and Mark rearranging him, dragging a folding chair over to prop his ass on, his torso resting over Derek's thighs. If he twists his head just a bit he can just lick up the side of Derek's cock. He gets in a few tastes before Derek is leaning down, giving him a messy kiss before directing Stiles’ attention down towards his own ass and whispering in his ear to stop them if he has a problem with what's going to happen next. Stiles quirks an eyebrow but pays attention to where Mark is kneeling next to the chair, taking the pillows the other guys are passing over and stacking them under Stiles’ ass until its tilted up above his body. Jackson is alternating between watching what's happening and fellating the toes that Derek had in Stiles’ ass earlier, trying to watch but also clearly not wanting to stop playing. It's weird. And hot. Weirdly hot. Stiles’ attention is dragged back to his own body when he feels a shock of cold against his hole - cold but not wet. He startles a bit, feels his hole clench shut as he directs his gaze a little better and sees Mark smiling and holding up the offending source. It's a fresh bottle of beer, condensation rolling down the sides. Stiles takes a breath before nodding his head slightly and doing his best to relax.
It's weirder than he expects when the mouth of the bottle slips inside him as it's tipped up. Even weirder when he feels his body start to suck the beer in. He can feel himself resisting and takes another breath, telling himself to just let go. Stiles starts rhythmically and carefully clenching his ass, mimicking the way his throat would move if he was drinking the beer. He's rewarded by the faster of flow of the liquid inside of him, filling him up from the wrong way. He can see the slosh of the remaining beer in the bottle, the blooms of air every time his hole relaxes and more chugs down into him. He doesn't know if he likes it or not, doesn't hate it, but it's...different. Stiles tries his best to remain mostly still, aside from the way his ass is rippling around the neck of the bottle, Mark still holding it in place. He can feel a gentle sweep on the underside of his arms where Derek is gripping him to brace his upper body. He watches for a little while longer before deciding it's too odd to watch and turning his face into Derek's crotch, doing his best to lick at Derek's cock some before trying to suck Derek's balls into his mouth. He's pretty sure he whines a little because he can feel Derek laughing beneath him and then one of his hands is dragging out from between them and lifting his hairy sac to put it in better range, pushing the bits that don't fit into Stiles’ mouth onto his face, rolling his palm over it all. Stiles’ mouth sucks as much at the nutsac as his ass does at the bottle in it, feeling full at both ends. It goes on for less than a minute longer before he can feel the bottle start to wiggle a bit as they demand his attention.
Jackson is hovering where Mark had been when Stiles finally gives up and releases Derek's balls. He can feel shifting behind him and more pressure as Jackson holds the bottle in place, not letting it slip from Stiles while someone new moves to brace his head so Derek can move around,standing behind where Jackson is kneeling, one of the handheld cameras zoomed in on where the bottle is sticking out of him. He can see the bottle is empty, feels the slosh of the beer inside him, an odd sensation in his ass - not exactly unpleasant, just weird. Derek's eyebrows raise at him slightly and he gives a tiny nod to indicate he's still okay with what's happening, even if he's not really sure what it is. He doesn't have to wait any longer to find out though as Jackson leans down, the handheld camera following his face when his tongue sweeps out to lick at Stiles’ rim where it's stretched around the bottle, lapping up the tiny trickles of beer that have begun to seep past the glass.
Stiles moans out, tried to fight his body's urge to clench down harder on the bottle, as Jackson licks and slurps at his rim. He can feel his hips twitching where they're braced, trying to push up into the sensation, groans when Jackson's teeth scrape at the over-sensitized muscle. Stiles almost doesn't notice when the bottle is gently wiggled, carefully being eased out of him. Jackson's ministrations keep up as he removed the bottle, his mouth shifting further towards center until his tongue buries itself in Stiles’ hole as the mouth of the bottle pops free, plugging him up. Stiles does his best to clamp down, hold the beer inside, as the guys work together to shuffle him around more. Jackson's mouth stays latched on as he kneels on the floor, Stiles’ legs shifted by the others so they're resting over Jackson's shoulders, his ass hanging off the edge of the folding chair now. Derek passes his handheld off to someone else - Stiles is having trouble focusing, attention firmly on keeping his ass tight around Jackson's tongue - and then his legs are being yanked further apart, hole spasming a bit and leaking more beer, as Derek shoulders in next to Jackson. Stiles can see 2 of the other guys standing over them, one panning a handheld from where Derek and Jackson are kneeling up Stiles’ body to his face and back down, the other maneuvering behind the guys to angle the viewfinder at his ass between their shoulders. It's distracting and takes him a minute to realize Derek is talking to him.
“C'mon baby, he's thirsty…relax that slutty hole for us.” Stiles can feel gentle pressure around his rim, a fingertrip probing beneath Jackson's list. “Just let go, pledge, give it to him, let us watch him drink from your tight little fuckhole and you'll be in.” He looks up and makes eye contact with Derek, sees the smirk on his face and takes a breath before relaxing his hole a little, writing when Jackson's moan vibrates through his ass as his mouth is flooded with beer. Stiles clenches up tight when Jackson pulls back, chin shiny with the liquid as he works to swallow the mouthful. He can feel more beer trickling out as Derek presses around his hole.
“Fuck that's hot.” Stiles isn't sure who says it, too focused on the sight below him, the way Derek is staring raptly at his ass, the hunger in his gaze, mirrored on Jackson's face.
“Push it out baby, come on, we're thirsty.” Derek's free hand pushes under him, angling his ass up a bit, hole pointed towards their faces as they shift as close as they can between his legs. Jackson reaches a hand up to mirror the one Derek still has near his hole, pulling him open as Derek does the same from the other side. Stiles takes a breath and then tries to relax his hole and bear down at the same time, feeling the liquid shoot out. He watches the first splashes hit their chins and chests before they both adjust so the stream is blasting at mouth level. His cock pulses and burns, aching for a hand on it and leaking precum as he watches them take turns putting their mouths in the line of the liquid gushing out of him, drinking it down and getting soaked in the process. He can hear the slick sounds of the other three guys jacking off as they watch.
The beer is trailing off to a trickle, still plenty sloshing inside him but no longer pushing out, when the first hot splatter of cum hits him in the face. He thinks it's from Mark, who he's finally figured out is the one bracing his head. Cam and Brian follow quickly after, painting his chin and cheeks with their own cum, clumping his eyelashes together with the sticky mess. He's given a minute before he can feel prodding at his hole again, quickly followed by a familiar cock filling him up in one smooth thrust. Stiles can feel the remnants of the beer pushing out around the intrusion, can't do much but writhe and moan and take it, Derek's hands clamped over his hips, the pace damn near brutal as he fucks in.
Stiles can't wait to see the video later, wishes he could watch now, see the way the beer would be frothing up and coating Derek's cock as it fucks in and out of him. It's fast and frantic and only takes a few minutes after all of them being keyed up for what feels like hours now, and then Derek's yanking out and straddling Stiles’ chest, stripping his cock, knuckles brushing against Stiles’ sternum before he grunts and spills over, adding to the mess coating Stiles’ face. He obliges easily when he feels a hand pulling at his mouth, opens and begins sucking when a wet and softening cock is thrust inside. He can taste beer and cum and the musky flavor of his own ass as Derek gently fucks into his mouth, making sure Stiles cleans him up. He draws back enough that only the hooded tip is still inside, lets Stiles suckle at it when he feels another cock pushing into his hole. He's pretty sure it's Jackson who's jackrabbiting inside him now, chasing his own orgasm. It's faster than Derek was, barely a minute before he's yanking back out and shooting all over Stiles’ still twitching hole. Derek lifts off of him as Jackson starts to crawl up his body until his mouth is wrapped around Stiles’ cock. It takes even less time for Stiles, Jackson sucking at the head, fingers nailing his prostate. Jackson pulls off just before Stiles blows his load, angling his cock so it shoots up his belly and chest.
Stiles is dazed but can feel Jackson move back, sees Cam and Brian panning the handhelds over him when he cracks his eyelids, trying not to get cum in them, fully taking in how covered in it he is. Jackson gives them a few seconds before he hovers back over, tongue laving up Stiles’ belly and chest, gathering the mess. He slurps at Stiles’ face too cleaning it and pulling Stiles’ mouth open, dripping a mouthful of spunk down into it, filthy for the camera before sealing his own mouth to Stiles’, passing the pungent mess back and forth between them. Stiles vaguely hears someone call cut, feels a warm washcloth gently wiping at his eyes, but Jackson is still on top of him, tongue still twining with Stiles’ own, body grinding against him despite them both being too sensitive for anything else right now. He opens his eyes when the washcloth is removed, happy to have them unstuck, sees Derek grinning at him and pushing Jackson's face back gently so he can sweep his own tongue through Stiles’ mouth.
“You were perfect today, both of you.” Stiles can see Jackson preen, see the slight flush on his cheeks. Opens his mouth to say something but doesn't get a word out before Jackson's mouth is on him again. He can hear Derek laugh before quietly whispering into Stiles’ ear that he can't wait to have Jackson in their bed outside of filming, and Stiles can't help but agree.